WO2007066512A1 - Triazasumanene et son procede de fabrication - Google Patents

Triazasumanene et son procede de fabrication Download PDF

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Publication number
WO2007066512A1
WO2007066512A1 PCT/JP2006/323287 JP2006323287W WO2007066512A1 WO 2007066512 A1 WO2007066512 A1 WO 2007066512A1 JP 2006323287 W JP2006323287 W JP 2006323287W WO 2007066512 A1 WO2007066512 A1 WO 2007066512A1
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formula
group
organic group
compound represented
same
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PCT/JP2006/323287
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English (en)
Japanese (ja)
Inventor
Hidehiro Sakurai
Shuhei Higashibayashi
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Inter-University Research Institute Corporation National Institutes Of Natural Sciences
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Publication of WO2007066512A1 publication Critical patent/WO2007066512A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
    • C07D471/16—Peri-condensed systems

Definitions

  • a group of 600 carbon dioxide (below, runns) is attracting attention as a potential next-generation material because of its different characteristics. It is known that the lans have a structure of C 60 or outside C 0, and each has its own unique characteristics. Research to add various functions by modifying them is also being actively carried out worldwide.
  • the lanthanides can be synthesized by the 000 synthesis method, the lanthanides can be easily introduced and the lanthanides of the lanthanides can be easily obtained by the easy conversion of the starting materials. It is considered possible to obtain modified lans, which was difficult. Furthermore, by providing a method for producing such chemically modified lans, it can be expected to bring about a significant impact on the total amount of new fees. For example, the behavior of lans in which some of the carbon atoms of lans have been replaced by children has attracted attention due to theoretical research ( ,) Is C (2) or C (2)
  • the child can be placed in the position of the tune, but the child could not be introduced into the case of.
  • ( ⁇ ), ⁇ are each independently a hydrogen atom or a monovalent gen, and may be the same or different, ⁇ 3
  • Is tin (C) the isomers thereof, the optical isomers thereof, and, in addition, those.
  • 3 The compound represented by (), its isomers, optical isomers, and those.
  • Each R is a hydrogen atom
  • R RL and R R are each independently hydrogen atoms
  • ((V), ⁇ are each independently divalent and are the same or different.
  • P ⁇ are each independently a monovalent hydrogen atom, and they may be the same or different.
  • a compound represented by 9 (V) its isomers, optical isomers, and those.
  • (( ⁇ ), ⁇ are each independently a hydrogen atom or a monovalent gen, and may be the same or different, ⁇ 3
  • ((V), ⁇ are each independently divalent, and may be the same or different, and P ⁇ are independently hydrogen atom-monovalent, and may be the same or different. You can.
  • ((V), ⁇ are each independently divalent and are the same or different.
  • P ⁇ are each independently a monovalent hydrogen atom, and they may be the same or different.
  • V (in V, represents divalent, P represents hydrogen atom, monovalent, X represents elementary atom, elementary atom, atom, C ", P (") or S, and " Aki, Aki, A A group.
  • Step 3 is a step of converting an ad group of the compound represented by the above (V) to obtain a product represented by the following (), and obtaining a product represented by the following (), a product represented by the above Process including the step 2, the product represented by ( ⁇ ), its isomers, optical isomers, and salts thereof.
  • 3 represents a monovalent and may be the same or different.
  • steps include the step of obtaining the compound represented by (V) below (the step of obtaining the product represented by crying, and the step of protecting the compound represented by the following () to obtain the product represented by the above (). Including those represented by 2), their isomers, optical isomers, and salts thereof.
  • P ⁇ are each independently a monovalent hydrogen atom, and they may be the same or different.
  • V is a compounding step in which the triplets of the compound represented by V are combined to obtain the product represented by the following (V), the following (depending on the reaction of the product represented by the V, A product represented by the following (V), an isomer, an optical isomer thereof, and a salt thereof, which is characterized by including the process of obtaining the product represented by the (V).
  • V (in V, represents divalent, P represents hydrogen atom, monovalent, X represents elementary atom, elementary atom, atom, C ", P (") or S
  • V (in V, represents divalent, P represents hydrogen atom and monovalent, X represents elementary atom, elementary atom, atom, C ", P (") or SC, and " Represents aki, achi, achi group.)
  • (( ⁇ ), ⁇ are each independently a hydrogen atom
  • the tonnesenes represent the compounds represented by the above formula, their isomers, optical isomers, and salts thereof.
  • In ( ⁇ ), is a hydrogen atom, a gen
  • Chlorine atom elementary atom, atom
  • monovalent Each may be one or different.
  • the monovalent in is an aki (preferably a prime number ⁇ 6, more preferably a prime number ⁇ 3, and particularly preferably a prime number ⁇ 2),
  • Aki (preferably prime number ⁇ 6, more preferably prime number ⁇ 3, especially preferably prime number ⁇ 2)
  • Aki (preferably prime number 6 ⁇ 6, more preferably prime number 6 ⁇ 3, Particularly preferred is an achi group having a prime number of 6 to 2), acebo (preferably a prime number of 2 to 3, more preferably a prime number of 2 to 2, and further preferably an ace group of 2 to 2).
  • avocado preferably prime number 7 to 3, more preferably prime number 7 2 and particularly preferably prime number 7 to 2 Aki group
  • 003 (preferably prime ⁇ 2, more preferably prime ⁇ 6, especially preferred prime ⁇ 2 ax group), as (preferably prime 6 ⁇ 2, more preferably Prime numbers 6 to 6, particularly preferably prime numbers 6 to 2 as the base, and axi (more preferably prime numbers to 2 more preferably prime numbers to 6 and particularly preferably prime numbers to 2)
  • a group an asphy (preferably a prime number of 6 to 2, more preferably a prime number of 6 to 6, and particularly preferably a prime number of 6 to 2), Hidoki, Cabo, Ano, To, hydra (preferably having 3 to 4 carbon atoms, more preferably having 3 to 3 carbon atoms, and particularly preferably having 3 to 24 carbon atoms), ki (more preferably having 3 to 6 carbon atoms, More preferably, it has a prime number of 3 to 4, and most preferably, it is a group having a carbon number of 3 to 24).
  • valences may have a substituent, or, when possible, may bond to each other to form a ring.
  • a may be or may be a heterocycle, and may be a or a polycycle.
  • Examples thereof include gen, alkene, oki (), (S), no (), hydrno () no (), etc. having the above valence.
  • a hydrogen atom As a hydrogen atom, a hydrogen atom, or a hydrogen atom, a hydrogen atom, a hydrogen atom, a hydrogen atom, or a hydrogen atom, which may have a substituent. Or, even if it has a substituent, it is more preferable that it is an acyl group, an acoxy group, a hydrogen atom, a substituted group, a substituted pyridic group, a carbon number of 2 to 5 Akobo or Hydomechi A group is more preferable, and a hydrogen atom is particularly preferable.
  • a hydrogen atom is particularly preferable.
  • ⁇ 3 may be one or different.
  • the valency represents a group having the following structures.
  • 003 is synonymous with the above R, and represents a hydrogen atom or a monovalent gen, and may be one or different.
  • the preferred range of aki, aki, aki, aki, aki, aki, aki, aki, aki, aki, akibo, akiabobo, aki, force ,,, in is the above value. Same as the preferred range in.
  • ??? in ??? is preferably a group represented by the above 36 or 7, more preferably ???, and most preferably methine (C).
  • the modified isomer is also included in the compound of the present invention.
  • the mutants in the clear product include the following products.
  • 004 is also an optically active substance represented by the symbol ⁇ .
  • biologically active forms the two biologically active forms of Tohsune are shown below.
  • the tousnes are optically active molecules that do not cause bow-bow bow sonson as shown below at around room temperature.
  • the calculation was performed by using the tones, and the numerator calculation using the calculation method 3 P 6 3 G.
  • the onion AG required for the Bow o Bow nve son is 366 ca, and the calculation results also suggest that the Bow o Bow nve son does not occur near room temperature.
  • the salt of the present invention forms a salt
  • the salt is also included in the scope of the present invention.
  • the salt is not particularly limited, and may be, for example, or.
  • the group to be formed may be an inorganic acid or an organic acid, and the group to be formed may be an inorganic group or an organic group.
  • the organic acid is not particularly limited, and examples thereof include sulfuric acid, phosphorus, hydrochloric acid, phosphoric acid, arsenic acid, hypochlorous acid, and (C) P Sb.
  • organic acids include, but are not limited to, carbon dioxide, sulfonic acid, and the like, and specifically, for example, phon, methanesulfone, tomomethanesulfone, u, carbonic acid, ku, kun, Benzoic acid ,.
  • Examples of the group include, but are not limited to, ammonium hydroxide, aka, carbonate and oxyhydrogen, and aka, carbonate and oxyhydrogen, and specific examples include , Sodium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, potassium hydroxide and the like.
  • the group includes, but is not particularly limited to, for example, and specifically, for example, tanoan, totinoanth (meth) anono. And the like.
  • the salt of Akira compound also includes a salt in which a plurality of atom atoms of the Akira compound are removed to form a monovalent polyvalent ion.
  • a counter cation of salt As a counter cation of salt
  • Each R is a hydrogen atom
  • 3 represents a monovalent and may be the same or different.
  • Each RLR is a hydrogen atom, a 2a 2
  • R R R R is b 2a 2b 3a 3b
  • Each R R R R is preferably a hydrogen atom gene.
  • the monovalent value in RRRR is synonymous with the monovalent value in the above ( ⁇ ), and the preferred range is also the same. 3 3 (In the screaming, ⁇ stands for each of the two values, and each of ⁇ may be one or different.
  • Valence has the same meaning as divalence in the above item (2), and the preferred range is also the same.
  • PS nO ganC nheS S (3 dEd n, The da ⁇ DG ⁇ eene and Pe e ⁇ G ⁇ M ⁇ s, We John ons line, 999) etc. are more preferable.
  • a benzyl-based protecting group is more preferable, and a benzyl and otometochitobenji (P) group is particularly preferable.
  • the salt is also included in the product of the present invention.
  • the salt is not particularly limited, and may be, for example, or.
  • the salt of the product represented by Akira also called screaming also includes a salt in which a plurality of elementary atoms of the product represented by Akira () are converted into monovalent and polyvalent aons.
  • Examples of the counter cation of the salt include L, a ",”, b “, Cs", “, Ca”, S 2 "a and the like.
  • P ⁇ are each independently a monovalent hydrogen atom, and they may be the same or different.
  • each of ⁇ stands for divalent. Also, ⁇ T may be one or different.
  • Valence has the same meaning as divalence in the above item (2), and the preferred range is also the same.
  • P to each represent a monovalent hydrogen atom. Also, P ⁇ 3
  • the isomer (denoted by () of Akira of Akira has isomers of the isomer, those isomers are also included in the isomer of (presented by cry.
  • the represented product has a variant as an equilibrium state, the modified isomer is also included in the product represented by () in the present invention.
  • the salt represented by () forms a salt
  • the salt is also included in the salt of the present invention.
  • the salt is not particularly limited, and may be, for example, the salt and the base are represented by the above formula. Stuffed with Can be used.
  • the salt of the product represented by () in Akira includes a salt obtained by cutting out a plurality of elementary atoms of the product represented by () in a monovalent and polyvalent ion.
  • each of ⁇ stands for a divalent group. Also, ⁇ 3
  • Valence has the same meaning as divalence in the above item (2), and the preferred range is also the same.
  • each of P ⁇ stands for a monovalent hydrogen atom.
  • P ⁇ may be one or different.
  • the salt is also included in the compound of the present invention.
  • the salt is not particularly limited, and may be, for example. You can use the one shown.
  • the salt of the substance represented by (V) of Ming includes the salt of monovalent polyvalent aon obtained by cutting out a plurality of element atoms of the substance represented by (V) of Ming.
  • Examples of the counter cation of the salt include, a ",”, b “, Cs", “, Ca” 2 and S "a.
  • the method for producing the salt of the bright substance for example, a method of adding the above-mentioned group to the bright substance by a public method, or a group of the bright substance being reacted with a hydrogen atom. There is a method of pulling out.
  • 005 the substance represented by (V), its isomers, optical isomers, and these
  • the compound represented by (V) in Ming is the following.
  • Stands for divalent may be one or different.
  • Valence has the same meaning as divalence in the above item (2), and the preferred range is also the same.
  • each of P ⁇ stands for a monovalent hydrogen atom.
  • P ⁇ may be one or different.
  • the monovalence in (V) is synonymous with the monovalence in the above-mentioned (P in exclamation), and the preferred range is also the same.
  • the salt is also included in the compound of this invention.
  • the salt is not particularly limited, and may be, for example, or.
  • the salt and the base the ones represented by the above formula (1) can be used.
  • the salt of the compound represented by (V) of Ming also includes a salt obtained by cutting out a plurality of elementary atoms of the product of (V) of the Ming to form a monovalent polyvalent ion.
  • the compounds represented by ( ⁇ ) to (V), their isomers, tautomers, optical isomers, and salts thereof have an element atom having Therefore, it can be easily metalized and a metal body can be formed.
  • Akira which is represented by ( ⁇ ) ⁇ (V), its isomers, tautomers, optical isomers, and salts thereof, including the antecedents on 2 and gold on 2
  • the child may form the body of. It may also have other arrangements than the above.
  • Other examples of the ion are, ion, and ion, which may be monovalent monovalent or polyvalent.
  • the core metal of the clear body is a substance represented by ( ⁇ ) ⁇ (V), its isomers, tautomers, optical isomers, and any metal capable of forming those isomers. There is no particular limitation, but it is preferably a transition (3 to in the period), more preferably an element and a lanthanide, and further preferably C (, d (, e () Y (1)). .
  • the aeon of the central metal in the clear body is not particularly limited as described above, but the on of the reactivity and the like (for example,
  • V (in V, represents divalent, P represents hydrogen atom, monovalent, X represents elementary atom, elementary atom, atom, C ", P (") or S, and " Represents achi, achi, achi group.
  • V is divalent
  • P is hydrogen atom monovalent
  • X is an elementary atom, an elementary atom, an atom, OC ", P (") or S And also represent achi, achi, achi.
  • Monovalent in P means P ⁇ 3 in (V) above.
  • Toki-Cabo Benji-Oki-Cabo (Z, 2 (Tomechi Toki-Cabo (OC), Aoki) Cabo (oc), 2 2 2 Tokutoki Cabo (oc), 9 Otoki Cabo (OC), (s) (s) groups are more preferred, and Tokio Cabo (oc) groups are I especially like it.
  • X is preferably a leaving substitution, more preferably a chlorine atom, an elementary atom, an atomic OS, more preferably a chlorine atom, an elementary atom, and an elementary atom. Is especially preferred.
  • the “2" in 2 may be either 1 or different.
  • V The substance represented by V includes its isomers, and includes, for example, the following isomers.
  • V 007 (V) or (V can be expressed as It can be manufactured by the method shown in.
  • the protector of Nokia 2 ⁇ 2 ⁇ Putane 3 is used, and the hydroxy group is used as acid cab.
  • the compound represented by the formula (V) or V can be obtained by a method of converting the obtained group into a halide by ao method via hydra, or a method of capturing the obtained carboxyl group as a node with a base. Obtainable. 007 3
  • reaction the following chemical reaction can be used, and examples thereof include Se.
  • the radical reaction the following method can be used, and examples thereof include E a o (De ekH R Ba one a Te ahed on Vo 44 p 147 1 62 1988) and the like.
  • the following method can be used as the reaction of the group. For example, a method in which CC ", CP ("), CS, and aquatic and aquatic compounds corresponding to these are acted on by the base. Is mentioned.
  • the body represented by (V) or (V) can be used, or the (kira) compound of optical power can be used.
  • the method of the product represented by the formula (V) or (V crying and the above method may be used even if a shining starting material is used, or a method such as Lakara reconnection at a different level. It may be divided by
  • the reaction may be carried out using, etc. to obtain the desired compound.
  • Sc e e3 An example of physical synthesis is shown below as Sc e e3, but is not limited to this.
  • the reaction using radium is more preferable.
  • one triplet it is possible to use 3 for transition and one for reaction in one pot, and to obtain C toluenes.
  • Examples of the applied reaction include the ec type, and reference can be made to Comp ehensve Oganome a cChems E ⁇ W Abe e a 1995). As shown in Sc e e4, due to the triplet represented by (V), 2 and 3 occur, which is the product represented by (V) (V A is obtained.
  • V A 007 8 is preferably radium, and more preferably radium sodium, although it is not particularly limited as long as the pungent reaction progresses.
  • the conditions under which the radium nuclei occur in the reaction system include, for example, Using rhodium (Pd (Oc)) with xanthine, adding tin (PP) to 2 and then adding tetrathium ammonium acetate (Oc) as the base and sodium as the base, Generate.
  • the group may be an inorganic group or an organic group as long as it is a group that can be used for a pendant reaction.
  • reaction time or the reaction frequency as long as the reaction proceeds.
  • the step of obtaining the product represented by the above (V) is carried out by adding the product of the above (V) to the product in the case of Ming.
  • An ad, a compound represented by (V) is formed by hydrolyzing the 3 ad group forming a ring in (V) to form a thermodynamically stable structure. It is a process of obtaining.
  • the product of (V) is more dynamic than the product of (V) because the cyclic adduct is in the ktenone position. It is stable, and after hydrolysis of 3 ring-forming adducts, the compound of formula (V) can be obtained by re-adding it under thermodynamic conditions. The outline of the process is shown in Sc e e5 below.
  • the method (1) may be used, and either acidic hydrolysis or basic hydrolysis may be used.
  • the method for water splitting and re-adding the method of is preferably used, but the method of activating and reacting boric acid is preferably used.
  • the method of activating and reacting boric acid is preferably used.
  • the method of activation with a synthetic substance is more preferable, and specifically, CC (NN Dc cohex cabod mde) or C (N (3 Dmeh amnop oP) N eh cabod mdoh d ocho de) is used as H d ox b enzo azoe) (7 Aza hd ox 23 benzo azoe) or the method of using sodium phosphine ((C) P () C) as the basic phosphate. Is more preferred.
  • the process in Ming is a process of obtaining the product represented by the above formula (V) from the product represented by the above formula.
  • the method for producing the compound represented by (V) is not particularly limited, but, for example, as shown in the following Sc e e6, the nitrogen atom on the nitrogen atom of the cyclic ad group in the product represented by the above (V) is Place P ⁇ 3
  • the protection method is not particularly limited, but it is preferable to use the method described in the above-mentioned P o ec veG o ps nO ganc nhes s.
  • the conversion method for the object represented by another expression ( ⁇ ) may be introduced.
  • the substitution method of the reaction at the 2-position of the gin ring can be referred to.
  • the step of obtaining the compound represented by the following (), in which the addition group of the compound represented by the above (V) is returned It is also preferable to include the step of obtaining a product.
  • Each R independently represents a hydrogen atom or a univalent gen, and may be the same or different, ⁇ 3
  • the following method can be used, and for example, a method using a reducing agent such as thallium borane is preferable.
  • the way to do things that are yelled is to use tetrazine.
  • the gin ring method can be used, for example, the method according to is preferred.
  • the following agents can be used, and quinone-based agents such as 2 3 Cu 5 6 anno 4 benzoquinone, metallic acids such as ammonium (V), Gold such as gangan diacid is preferable.
  • A) (1 B), which has good stability in air, is a material that is expressed by formula ( ⁇ ) and is distorted by oxygen by oxygen, and ( ⁇ ) The thing represented by and the thing represented by ().
  • the above step is a step of converting the compound represented by the above (V) to obtain a compound represented by the following (11), It is also preferable to include the step of obtaining the compound represented by ( ⁇ ).
  • the following method can be used. As shown in the following Sc e8, the method for directly converting the compound represented by (V), The method of introducing and at the position of the ad group in the compound represented by V) can be preferably used.
  • P ⁇ may be replaced, or may be replaced, or optics may be performed.
  • Step 3 and ad are synonymous with step 3 and ad in the method for producing the above-mentioned tonnes, and are the same as the preferred method.
  • step 3 synonymous with step 3 in the method for producing the above-mentioned tones, and the same as the preferred method.
  • the position P ⁇ on the nitrogen atom of the cyclic ad group may be replaced with another P ⁇ , the compound may be replaced with, or the optical ratio may be determined. 0100, the explanation will be specifically explained based on the implementation, but it is not limited to the implementation.
  • the inorganic substances used were those produced by Laitesque Co., Ltd., and the related substances used were those produced by Tokyo Co., Ltd.
  • AnO dResea ch s ems M A 00 was used to determine the points.
  • a COP 020 from JASCO Corporation was used to determine the light intensity.
  • a COFT R 400 from JASCO Corporation was used for the determination of the spectrum.
  • EO JM 777V of JEOL Ltd. was used to determine the spectrum.
  • Gin P 545 4.46 o was added and O was added at room temperature.
  • This adduct was dissolved in methane (21), and benzoic acid (CP 3 4 53 5 o) at 69 ° C was added at room temperature. After decompressing methane, water was added and the mixture was discharged with a chi ().
  • the solution was treated with sodium solution (), () and saturated saline, dried over anhydrous sodium sulfate and filtered through Celite. Decompression was carried out to obtain a po.
  • the three quantone carbons were prepared according to: ⁇ O g Che 984 Vo 49 p ⁇ 928 931. In addition, 3 quant carbon is also sold by d c and others.
  • the methano (5) of hydra was added to the methano (3) of g o) at 2 C. After adding water, I took out at Chi (3). The extract was dried over water and saturated brine, dried over anhydrous sodium sulfate, and then decompressed organically to obtain a crude product.
  • Hexane, (22) is heated to C, (4S) 6 (528 ⁇ 7 o) 4 xane (81), radium (Pd (c) 9 2 O 86).
  • Oxane (4) (4) (4) was added, and the mixture was diluted with C (5). The solution was filtered with a light and a lizard, and the organic pressure was reduced. The product was made from Kagekara Tokugra (thixane 65 35) to obtain (4S 5 8S g 2S) 7 (436).
  • Token 9 is used as a transition medium and hydrogen as an oxidative reaction to replace the 3 atoms in Token 9 with hydrogen. You can get a tune 2.
  • the following method can be used, and an example thereof is the method described in B Koean Che Soc. 21 211 214 (1999).
  • the protective body can be subjected to a oxidization reaction, followed by a oxidization reaction. Makes it possible to introduce substitution at the nitrogen atom position on the pyridine.
  • the metal forming method can be used to form a metal body in which metal particles are arranged in the solder.
  • Examples of genera include C (), Pd (), Ce (), and b ().

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L’invention concerne un triazasumanène et son procédé de fabrication. Le triazasumanène selon la présente invention et son procédé de fabrication désignent des composés spécifiques représentés par les formules (I) à (V) ci-dessous, leurs stéréoisomères, leurs isomères optiques et leurs racémates, les sels de ces composés, ainsi que leurs procédés de fabrication. Dans les formules ci-dessous, R1 à R3 représentent indépendamment un atome d’hydrogène, un atome d’halogène ou un groupement organique monovalent ; L1 à L3 représentent indépendamment un groupement organique bivalent ; R1a, R1b, R2a, R2b, R3a et R3b représentent indépendamment un atome d’hydrogène, un atome d’halogène ou un groupement organique monovalent ; et P1 à P3 représentent indépendamment un atome d’hydrogène ou un groupement organique monovalent. (I) (II) (III) (IV) (V)
PCT/JP2006/323287 2005-12-05 2006-11-22 Triazasumanene et son procede de fabrication WO2007066512A1 (fr)

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JP2005350574A JP2009046392A (ja) 2005-12-05 2005-12-05 トリアザスマネン類、及び、その製造方法
JP2005-350574 2005-12-05

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004067446A2 (fr) * 2003-01-31 2004-08-12 Osaka Ind Promotion Org Sumanene et procede de fabrication de celui-ci
JP2006076995A (ja) * 2004-07-30 2006-03-23 Osaka Univ 有機半導体およびそれを用いた電子機器

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004067446A2 (fr) * 2003-01-31 2004-08-12 Osaka Ind Promotion Org Sumanene et procede de fabrication de celui-ci
JP2006076995A (ja) * 2004-07-30 2006-03-23 Osaka Univ 有機半導体およびそれを用いた電子機器

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
BUEHL M.: "C54N6, a potentially aromatic molecule", CHEMICAL PHYSICS LETTERS, vol. 242, no. 6, 1995, pages 580 - 584, XP000573573 *

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